Trifluoroacetic acid → HCID 59547282, compound

HRID 2038557Notes

Reaction equation

HRID 2038557 reaction equation
[CH:1]1([CH2:7][C:8]([NH:10][C@@H:11]([C:37]([CH3:40])([CH3:39])[CH3:38])[C:12]([N:14]2[C@H:29]([C:30]([O:32]C(C)(C)C)=[O:31])[CH2:28][C@:16]3([O:20][C:19](=[O:21])[N:18]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH2:17]3)[CH2:15]2)=[O:13])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:1]1([CH2:7][C:8]([NH:10][C@@H:11]([C:37]([CH3:40])([CH3:39])[CH3:38])[C:12]([N:14]2[C@H:29]([C:30]([OH:32])=[O:31])[CH2:28][C@:16]3([O:20][C:19](=[O:21])[N:18]([C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH2:17]3)[CH2:15]2)=[O:13])=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59547344HCID 59547344, compound

Product 1

HCID 59547282HCID 59547282, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(5S,8S)-tert-butyl 7-((S)-2-(2-cyclohexylacetamido)-3,3-dimethylbutanoyl)-2-oxo-3-phenyl-1-oxa-3,7-diazaspiro[4.4]nonane-8-carboxylate (G1) (70 mg, 126 μmol, 1 eq.) was diluted in 1:1 DCM:TFA (2 mL) and stirred overnight at room temp. then concentrated to give (5S,8S)-7-((S)-2-(2-cyclohexylacetamido)-3,3-dimethylbutanoyl)-2-oxo-3-phenyl-1-oxa-3,7-diazaspiro[4.4]nonane-8-carboxylic acid (H1) in quantitative yield. LC MS+/−: 500.41/498.55 at 3.09 min (10-90%, 3-5 min, Formic Acid).

Workup

  1. concentrationthen concentrated

Sources & evidence

ORD record
ord-759e5f2f9f024c76a5abb68f1161ff01
Source dataset
uspto-grants-2013_11
Patent number
US08575208B2

Reaction notes

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